Domino Ring‐Opening of <i>N</i>‐Tosyl Vinylaziridines Triggered by Aryne Diels‐Alder Reaction

Liu, Jiupeng; Li, Jiaqi; Ren, Bowen; Zhang, Yun; Xue, Linyi; Wang, Yanying; Zhao, Jingjing; Zhang, Puyu; Xu, Xuejun; Li, Pan

doi:10.1002/adsc.202100697

Cited by 11 publications

(2 citation statements)

References 67 publications

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“…27 A further aryne cascade process employing an alkene ene reaction was recently reported by Liu et al (Scheme 8c & d). 28 Upon exposure to excess aryne, N-tosyl vinylaziridines 38 undergo a sequential Diels-Alder cycloaddition, ring-opening aromatisation, ene reaction and final N-arylation to afford 2-(phenanthrene-9-yl)ethan-1-sulfamides 40. It was found that switching reaction conditions from CsF in acetonitrile to KF and 18-crown-6 ether in 1,4-dioxane prevented the final N-arylation stage.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Elsewhere, the groups of Minuti, Biju, Chenoweth, and Liu have reported alkene ene reactions involving larger polycyclic hydrocarbon systems. [25][26][27][28] In 1999, Minuti et al used benzyne, generated from diazotisation and subsequent thermal decomposition of anthranilic acid, to produce an arylated pentahelicene. 25 In 2014, Biju and coworkers treated a range of styrenes 32 with o-trimethylsilylaryl triflate 20, in the presence of a fluoride source, to furnish 9-aryldihydrophenanthrenes 34 through the incorporation of two equivalents of aryne (Scheme 8a).…”

Section: Short Review Synthesismentioning

confidence: 99%

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The Aryne Ene Reaction

Yang¹,

Jones²

2022

Synthesis

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Intermolecular aryne ene reactions present opportunities to arylate a wide range of unsaturated substrates in a single step, whilst intramolecular reactions provide expedient access to valuable benzofused carbo- and heterocyclic frameworks. This short review will chart the development of the aryne ene reaction from initial reports that rationalise unexpected by-product formation in competing [4+2] and [2+2] cycloadditions through to its exploitation in contemporary synthetic methodology.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Short Review Synthesismentioning

confidence: 99%

The Aryne Ene Reaction

Yang¹,

Jones²

2022

Synthesis

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Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Kim,

Choi,

Suh

et al. 2024

Chem. Rev.

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Arynes hold significance for the efficient fusion of (hetero) arenes with diverse substrates, advancing the construction of complex molecular frameworks. Employing multiple equivalents of arynes is particularly effective in the rapid formation of polycyclic cores found in optoelectronic materials and bioactive compounds. However, the inherent reactivity of arynes often leads to side reactions, yielding unanticipated products and underlining the importance of a detailed investigation into the use of multiple arynes to fine-tune their reactivity. This review centers on methodologies and syntheses in organic reactions involving multiple arynes, categorizing based on mechanisms like cycloadditions, σ-bond insertions, nucleophilic additions, and ene reactions, and discusses aryne polymerization. The categorization based on these mechanisms includes two primary approaches: the first entails multiple aryne engagement within a single step while the second approach involves using a single equivalent of aryne sequentially across multiple steps, with both requiring strict reactivity control to ensure precise aryne participation in each respective step. Additionally, the review provides an in-depth analysis of the selection of aryne precursors, organized chronologically and by activation strategy, offering a comprehensive background that supports the main theme of multiple aryne utilization. The expectation remains that this comprehensive review will be invaluable in designing advanced syntheses engaging multiple arynes.

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Merging Gold/Copper Catalysis and Copper/Photoredox Catalysis: An Approach to Alkyl Oxazoles from N-Propargylamides

et al. 2021

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Here, we report a mild and highly efficient approach to alkyl oxazoles through merging gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles are synthesized from N-propargylamides with alkyl halides in good to excellent yields with wide functional-group compatibility under blue-light irradiation. Significantly, a copper catalyst plays a dual role in this transformation: as a powerful cocatalyst to accelerate protodeauration of vinyl gold intermediates and improve photoredox catalysis.

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Domino Ring‐Opening of N‐Tosyl Vinylaziridines Triggered by Aryne Diels‐Alder Reaction

Cited by 11 publications

References 67 publications

The Aryne Ene Reaction

The Aryne Ene Reaction

Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Merging Gold/Copper Catalysis and Copper/Photoredox Catalysis: An Approach to Alkyl Oxazoles from N-Propargylamides

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